The influence of parenting skills on adolescent outcomes among children affected by maternal HIV/AIDS (N = 118, M age = 13) was investigated. Among families with more frequent family routines, over time adolescents showed lower rates of aggression, anxiety, worry, depression, conduct disorder, binge drinking, and increased self-concept. Among families with higher levels of parental monitoring, adolescents showed significant declines in anxiety and depression, conduct disorder, and binge drinking, along with increased self-concept. Mothers' level of illness was associated with parenting. Greater variability in parental monitoring resulted in higher levels of problem behaviors.